반응 #159986

반응 방정식

[[[(1,1-dimethylethoxy)carbonyl]amino]-(methylthio)methylene]-carbamic acid, 1,1-dimethylethyl ester

thiomorpholine

Et3N

methanethiol

→

(tert-Butoxycarbonylimino-thiomorpholin-4-yl-methyl)-carbamic acid tert-butyl ester

용매

DMF

EtOAc

반응 조건

후처리

1. 1
   여과filtered through a pad of diatomaceous earth
2. 2
   농축The filtrate was concentrated
3. 3
   workup.ADDITIONdiluted with water and EtOAc
4. 4
   여과filtered again through a pad of diatomaceous earth
5. 5
   기타The filtrate aqueous layer was separated
6. 6
   추출extracted with EtOAc (2×)
7. 7
   세척The combined organic layers were washed with water
8. 8
   건조aq. NaCl, dried
9. 9
   농축concentrated
10. 10
    기타The solid was triturated with 20% Et2O/40-60° C. petrol
11. 11
    여과The solid was filtered off
12. 12
    세척was washed with 20% Et2O/40-60° C. petrol
13. 13
    기타followed by 40-60° C.
14. 14
    기타The solid was dried under vacuum
15. 15
    기타to give 21.2 g (85%) as a white solid

실험 절차

A solution of [[[(1,1-dimethylethoxy)carbonyl]amino]-(methylthio)methylene]-carbamic acid, 1,1-dimethylethyl ester [CAS 107819-90-9] (21 g, 0.0723 mol) in DMF (450 mL) was treated sequentially with thiomorpholine (7 mL, 0.0723 mol), mercury chloride (19.6 g, 0.0723 mol), and Et3N (30 mL, 0.22 mol) and the reaction mixture was stirred for 18 h. The mixture was diluted with EtOAc and filtered through a pad of diatomaceous earth. The filtrate was concentrated, diluted with water and EtOAc and filtered again through a pad of diatomaceous earth. The filtrate aqueous layer was separated and extracted with EtOAc (2×). The combined organic layers were washed with water, then satd. aq. NaCl, dried, and concentrated. The solid was triturated with 20% Et2O/40-60° C. petrol. The solid was filtered off and was washed with 20% Et2O/40-60° C. petrol followed by 40-60° C. petrol. The solid was dried under vacuum to give 21.2 g (85%) as a white solid. Note: The reaction was performed with a trap for gaseous loss of methanethiol.

출처